Ethyl chloroformate → 4,4,4-Trifluoro-2-(triphenyl-lambda5-phosphanylidene)-butyric acid ethyl ester
반응식
[I-].[F:2][C:3]([F:26])([F:25])[CH2:4][CH2:5][P+:6]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:37]([O:39][C:40](Cl)=[O:41])[CH3:38]>C1COCC1>[CH2:37]([O:39][C:40](=[O:41])[C:5](=[P:6]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:4][C:3]([F:2])([F:25])[F:26])[CH3:38]참가 물질
반응 조건
- 온도
- -78 °C
실험 절차
To a suspension of (3,3,3-trifluoropropyl)-triphenylphosphonium iodide (105 g, 20.6 mmol) in THF (40 mL) at −78° C. was added slowly a solution of lithium bis(trimethylsilyl)amide (1.0 M in THF, 41.2 mL) through an addition funnel under nitrogen. The resulting mixture was stirred at −78° C. for 15 min followed by dropwise addition of a solution of ethylchloroformate (3.92 mL, 41.2 mmol) in THF (40 mL). The reaction mixture was then allowed to warm up to 25° C. while stirring. The reaction mixture was partitioned between EtOAc (300 mL) and brine (300 mL). The organic layer was dried over Na2SO4 and evaporated in vacuo to afford a crude solid which was purified by flash chromatography (EtOAc:hexanes 1:1) to provide a light tan solid (7.18 g) in 81% yield. Mass Spectrum (+ESI): 431 [M+H]+.
후처리
- temperatureto warm up to 25° C.
- stirringwhile stirring
- customThe reaction mixture was partitioned between EtOAc (300 mL) and brine (300 mL)
- dry with materialThe organic layer was dried over Na2SO4
- customevaporated in vacuo
- customto afford a crude solid which
- customwas purified by flash chromatography (EtOAc:hexanes 1:1)
출처 및 근거
- ORD 기록
- ord-f5d7aa0286af4165a1a02e2eec9aa7ee
- 출처 데이터셋
- uspto-grants-2009_06
- 특허 번호
- US07550629B2
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